TWI357897B - 3-substituted-5- and 6-aminoalkyl indole-2-carboxy - Google Patents

3-substituted-5- and 6-aminoalkyl indole-2-carboxy Download PDF

Info

Publication number: TWI357897B
Authority: TW; Taiwan
Prior art keywords: phenylthio; indole; carboxamide; group; compound
Prior art date: 2004-08-19

Application number

TW094128283A

Other languages

English (en)

Chinese (zh)

Other versions

TW200621711A (en

Inventor

Metz, Jr

Fa-Xiang Ding

Original Assignee

Aventis Pharma Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2004-08-19

Filing date

2005-08-19

Publication date

2012-02-11

2005-08-19 Application filed by Aventis Pharma Inc filed Critical Aventis Pharma Inc

2006-07-01 Publication of TW200621711A publication Critical patent/TW200621711A/zh

2012-02-11 Application granted granted Critical

2012-02-11 Publication of TWI357897B publication Critical patent/TWI357897B/zh

Links

-1 aminomethanyl Chemical group 0.000 claims description 277
150000001875 compounds Chemical class 0.000 claims description 140
125000000217 alkyl group Chemical group 0.000 claims description 84
125000000623 heterocyclic group Chemical group 0.000 claims description 81
125000003118 aryl group Chemical group 0.000 claims description 66
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 61
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 52
230000027288 circadian rhythm Effects 0.000 claims description 40
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 38
239000000203 mixture Substances 0.000 claims description 38
125000001041 indolyl group Chemical group 0.000 claims description 36
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
150000001412 amines Chemical class 0.000 claims description 32
230000007958 sleep Effects 0.000 claims description 28
208000019116 sleep disease Diseases 0.000 claims description 27
230000000694 effects Effects 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 25
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 23
125000003342 alkenyl group Chemical group 0.000 claims description 22
201000010099 disease Diseases 0.000 claims description 22
208000020925 Bipolar disease Diseases 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 16
208000035475 disorder Diseases 0.000 claims description 16
239000008194 pharmaceutical composition Substances 0.000 claims description 16
229910052757 nitrogen Inorganic materials 0.000 claims description 14
208000020685 sleep-wake disease Diseases 0.000 claims description 14
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 13
150000003857 carboxamides Chemical class 0.000 claims description 13
108010031425 Casein Kinases Proteins 0.000 claims description 12
102000005403 Casein Kinases Human genes 0.000 claims description 12
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
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229910052717 sulfur Inorganic materials 0.000 claims description 12
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125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
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IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
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PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 9
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 8
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 5
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125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 4
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230000035479 physiological effects, processes and functions Effects 0.000 claims description 4
125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims description 3
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CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims 1
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DAAPUDXKYYZXKS-UHFFFAOYSA-N 5-[(heptylamino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C12=CC(CNCCCCCCC)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 DAAPUDXKYYZXKS-UHFFFAOYSA-N 0.000 claims 1
UBDHSURDYAETAL-UHFFFAOYSA-N 8-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 UBDHSURDYAETAL-UHFFFAOYSA-N 0.000 claims 1
CKLJMWTZIZZHCS-UHFFFAOYSA-N Aspartic acid Chemical compound OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims 1
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150000001336 alkenes Chemical class 0.000 claims 1
229940125904 compound 1 Drugs 0.000 claims 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
125000006308 propyl amino group Chemical group 0.000 claims 1
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 87
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POOSGDOYLQNASK-UHFFFAOYSA-N tetracosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC POOSGDOYLQNASK-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
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Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Anesthesiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)

TW094128283A 2004-08-19 2005-08-19 3-substituted-5- and 6-aminoalkyl indole-2-carboxy TWI357897B (en)

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US60338004P	2004-08-19	2004-08-19

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TW200621711A TW200621711A (en)	2006-07-01
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US (2)	US7629376B2 (pt)
EP (1)	EP1794122B1 (pt)
JP (1)	JP4843608B2 (pt)
KR (2)	KR20070043012A (pt)
CN (1)	CN101006055B (pt)
AR (1)	AR050919A1 (pt)
AT (1)	ATE508112T1 (pt)
AU (1)	AU2005277523B2 (pt)
BR (1)	BRPI0514380A (pt)
CA (1)	CA2577667C (pt)
DE (1)	DE602005027858D1 (pt)
GT (1)	GT200500214A (pt)
IL (1)	IL181156A (pt)
JO (1)	JO2724B1 (pt)
MA (1)	MA28863B1 (pt)
MX (1)	MX2007001382A (pt)
NO (1)	NO20071466L (pt)
NZ (1)	NZ552800A (pt)
PA (1)	PA8642901A1 (pt)
PE (1)	PE20060498A1 (pt)
RU (1)	RU2369599C2 (pt)
SV (1)	SV2006002192A (pt)
TW (1)	TWI357897B (pt)
UY (1)	UY29078A1 (pt)
WO (1)	WO2006023467A1 (pt)
ZA (1)	ZA200700651B (pt)

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JP4748823B2 (ja)	2009-02-12	2011-08-17	株式会社ファルマデザイン	カゼインキナーゼ１δ及びカゼインキナーゼ１ε阻害剤
BRPI1016185A2 (pt) *	2009-04-17	2016-04-19	Cylene Pharmaceuticals Inc	processo para o tratamento de distúrbios associados à atividade da proteína quinase ck2
AU2013283318B2 (en)	2012-06-27	2017-11-23	4Sc Ag	Bifluorodioxalane-amino-benzimidazole kinase inhibitors for the treatment of cancer, autoimmuneinflammation and CNS disorders
JP2021511364A (ja)	2018-01-29	2021-05-06	カディラヘルスケアリミティド	抗菌剤として有用な複素環式化合物
WO2022006377A2 (en) *	2020-07-02	2022-01-06	Mbq Pharma	Heterocyclic inhibitors of rho gtpases for the treatment of disease
US12209078B2 (en)	2021-10-06	2025-01-28	Mbq Pharma	Crystalline forms of carbazole inhibitors of RhoGTPase for the treatment of disease

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US5296471A (en)	1992-12-22	1994-03-22	Glycomed Incorporated	Method for controlling o-desulfation of heparin and compositions produced thereby
DE60026998T2 (de) *	1999-06-08	2007-04-05	Aventis Pharmaceuticals Inc.	Screeningsverfahren zur änderung zirkadiane-rhythmus-eiweisse
CN1249051C (zh) *	2000-04-28	2006-04-05	阿卡蒂亚药品公司	毒蕈碱性激动剂
WO2004014851A2 (en) *	2002-08-09	2004-02-19	Merck & Co., Inc.	Tyrosine kinase inhibitors
DE602004020685D1 (de) *	2003-12-11	2009-05-28	Aventis Pharma Inc	Substituierte 1h-pyrroloä3,2-b, 3,2-c und 2,3-cüpyridin-2-carbonsäureamide und verwandte analoga als inhibitoren von caseinkinase-i-epsilon

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Also Published As

Publication number	Publication date
NO20071466L (no)	2007-04-19
BRPI0514380A (pt)	2008-06-10
EP1794122A1 (en)	2007-06-13
PE20060498A1 (es)	2006-07-10
MA28863B1 (fr)	2007-09-03
TW200621711A (en)	2006-07-01
CN101006055A (zh)	2007-07-25
AU2005277523B2 (en)	2011-09-29
SV2006002192A (es)	2006-06-28
CN101006055B (zh)	2011-06-22
US20080027124A1 (en)	2008-01-31
DE602005027858D1 (de)	2011-06-16
RU2369599C2 (ru)	2009-10-10
CA2577667A1 (en)	2006-03-02
RU2007109783A (ru)	2008-09-27
EP1794122B1 (en)	2011-05-04
IL181156A (en)	2011-09-27
PA8642901A1 (es)	2006-05-16
JP4843608B2 (ja)	2011-12-21
ZA200700651B (en)	2008-09-25
WO2006023467A1 (en)	2006-03-02
ATE508112T1 (de)	2011-05-15
JO2724B1 (en)	2013-09-15
KR20070043012A (ko)	2007-04-24
NZ552800A (en)	2010-11-26
US20090082340A1 (en)	2009-03-26
US7629376B2 (en)	2009-12-08
AR050919A1 (es)	2006-12-06
AU2005277523A1 (en)	2006-03-02
JP2008510017A (ja)	2008-04-03
CA2577667C (en)	2011-01-04
GT200500214A (es)	2006-03-27
MX2007001382A (es)	2007-04-19
UY29078A1 (es)	2006-03-31
US7923466B2 (en)	2011-04-12
KR20130038409A (ko)	2013-04-17
IL181156A0 (en)	2007-07-04
HK1105196A1 (en)	2008-02-06

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